ATE143367T1 - METHOD FOR PRODUCING OPTICALLY ACTIVE 2-ALKYL-2,5-DIAZABICYCLO(2.2.1>HEPTANES - Google Patents
METHOD FOR PRODUCING OPTICALLY ACTIVE 2-ALKYL-2,5-DIAZABICYCLO(2.2.1>HEPTANESInfo
- Publication number
- ATE143367T1 ATE143367T1 AT90310239T AT90310239T ATE143367T1 AT E143367 T1 ATE143367 T1 AT E143367T1 AT 90310239 T AT90310239 T AT 90310239T AT 90310239 T AT90310239 T AT 90310239T AT E143367 T1 ATE143367 T1 AT E143367T1
- Authority
- AT
- Austria
- Prior art keywords
- alkyl
- heptanes
- diazabicyclo
- optically active
- producing optically
- Prior art date
Links
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title 2
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000007660 quinolones Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- PMMYEEVYMWASQN-IMJSIDKUSA-N trans-4-Hydroxy-L-proline Natural products O[C@@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-IMJSIDKUSA-N 0.000 abstract 1
- PMMYEEVYMWASQN-IUYQGCFVSA-N trans-4-hydroxy-D-proline Chemical compound O[C@@H]1CN[C@@H](C(O)=O)C1 PMMYEEVYMWASQN-IUYQGCFVSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1S,4S and 1R,4R-2-Alkyl-2,5-diazabicyclo[2.2.1]-heptanes of the relative or absolute stereochemical formula (I) useful as intermediates in the synthesis of certain antibacterial quinolones, are prepared respectively, from trans-4-hydroxy-L-proline and trans-4-hydroxy-D-proline of the relative or absolute stereochemical formula (II) via multistep procedures. <CHEM> wherein R is (C1-C6)alkyl: R<2> is (C1-C6)alkyl,trifluoromethyl or <CHEM> S
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41207289A | 1989-09-25 | 1989-09-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE143367T1 true ATE143367T1 (en) | 1996-10-15 |
Family
ID=23631485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT90310239T ATE143367T1 (en) | 1989-09-25 | 1990-09-19 | METHOD FOR PRODUCING OPTICALLY ACTIVE 2-ALKYL-2,5-DIAZABICYCLO(2.2.1>HEPTANES |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP0420487B1 (en) |
| JP (1) | JPH0686452B2 (en) |
| AT (1) | ATE143367T1 (en) |
| CA (1) | CA2025959C (en) |
| DE (1) | DE69028673T2 (en) |
| DK (1) | DK0420487T3 (en) |
| ES (1) | ES2091802T3 (en) |
| FI (1) | FI93547C (en) |
| GR (1) | GR3021548T3 (en) |
| IE (1) | IE75360B1 (en) |
| PT (1) | PT95402B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116606235A (en) * | 2023-05-26 | 2023-08-18 | 南通敏言生物医药科技有限公司 | Synthesis method of (R) - (1-methylpyrrolidine-2-yl) methylamine dihydrochloride |
-
1990
- 1990-09-19 DK DK90310239.0T patent/DK0420487T3/en active
- 1990-09-19 DE DE69028673T patent/DE69028673T2/en not_active Expired - Fee Related
- 1990-09-19 AT AT90310239T patent/ATE143367T1/en not_active IP Right Cessation
- 1990-09-19 EP EP90310239A patent/EP0420487B1/en not_active Expired - Lifetime
- 1990-09-19 ES ES90310239T patent/ES2091802T3/en not_active Expired - Lifetime
- 1990-09-21 CA CA002025959A patent/CA2025959C/en not_active Expired - Lifetime
- 1990-09-24 PT PT95402A patent/PT95402B/en not_active IP Right Cessation
- 1990-09-24 FI FI904686A patent/FI93547C/en active IP Right Grant
- 1990-09-24 IE IE342490A patent/IE75360B1/en not_active IP Right Cessation
- 1990-09-25 JP JP2255029A patent/JPH0686452B2/en not_active Expired - Fee Related
-
1996
- 1996-11-06 GR GR960402922T patent/GR3021548T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0686452B2 (en) | 1994-11-02 |
| ES2091802T3 (en) | 1996-11-16 |
| EP0420487A3 (en) | 1991-11-27 |
| IE903424A1 (en) | 1991-04-10 |
| CA2025959C (en) | 1995-11-28 |
| DE69028673T2 (en) | 1997-02-20 |
| PT95402A (en) | 1991-05-22 |
| CA2025959A1 (en) | 1991-03-26 |
| FI93547B (en) | 1995-01-13 |
| EP0420487A2 (en) | 1991-04-03 |
| FI93547C (en) | 1995-04-25 |
| GR3021548T3 (en) | 1997-02-28 |
| DK0420487T3 (en) | 1997-03-17 |
| PT95402B (en) | 1997-07-31 |
| JPH03130285A (en) | 1991-06-04 |
| FI904686A0 (en) | 1990-09-24 |
| DE69028673D1 (en) | 1996-10-31 |
| EP0420487B1 (en) | 1996-09-25 |
| IE75360B1 (en) | 1997-08-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |